This invention relates to a process for the preparation of 2-fluoro-2-nitro-1,3-propanediol which is useful for formulation of explosives and propellants and as a precursor for the production of 3-fluoro-3-nitrooxetane and nitro polyethers.
2-Fluoro-2-nitro-1,3-propanediol has been prepared in low yields by fluorination of the cyclic ketal salt ##STR1## by L. W. Kissinger and T. M. Benziger and R. K. Rohner as reported in a book entitled "Nitro Compounds" which was put out by Tetrahedron (Vol. 20., Suppl. 1) in 1964. The article is entitled "The Action of polyphosphoric Acid on 2-Nitro-1,3-Propanediols and Some of Their Carbonate, Sulphite and 1,3-Dioxane Derivatives" and appears on p. 320 of the aforementioned book. The compound also may be prepared by fluorination of 2-sodium-2-nitro-1,3-propanediol in water or ethanol. The first method produces low yields and the second must be done slowly to prevent firing or charing. Both methods are impractical for large scale production.
Alternate possible methods of preparation would include aldol condensations of aldehydes with nitroalkanes as shown in U.S. Pat. Nos. 3,658,921 and 3,711,561 but this method appears to be impractical on a large scale.